1-Methylpiperazine → HCID 13298530, compound

HRID 1263221Notes

Reaction equation

HRID 1263221 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C(O)CCC>[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:2]2[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 27827912-Chloro-3-fluoropyridine

Product 1

HCID 13298530HCID 13298530, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2-chloro-3-fluoropyridine (1.0 g, 8.5 mmol) and N-methyl piperazine (4.26 g, 42.5 mmol) in n-butanol, 50 ml, is stirred at reflux for 18 hours. After concentrating under reduced pressure at 50° C., the residue is partitioned between ethyl ether and 50% NaOH solution. The ethyl ether extract is washed with a saturated sodium chloride solution, dried over Na2SO4, filtered and concentrated under reduced pressure. The oily product is converted to the hydrogen fumarate salt, mp 148°-149° C., by treatment with fumaric acid in methanol and precipitation with ethyl ether.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationAfter concentrating under reduced pressure at 50° C.
  3. customthe residue is partitioned between ethyl ether and 50% NaOH solution
  4. extractionThe ethyl ether extract
  5. washis washed with a saturated sodium chloride solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe oily product is converted to the hydrogen fumarate salt, mp 148°-149° C., by treatment with fumaric acid in methanol and precipitation with ethyl ether

Sources & evidence

ORD record
ord-c04ddd2be9c849f2b19cc410597fa44d
Source dataset
uspto-grants-1984_06
Patent number
US04456604

Reaction notes

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